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Compare 235 Vacation Homes in Ashland with updated reviews, rates, and availability.

"Great spot. Loved the fenced in yard for the dog and toddler. Parking easy. Felt safe. The house was spacious, clean, with comfortable beds. "

SAR 631 total

includes taxes & fees

26 Nov - 27 Nov

"Came in town for a race event house was clean and organized."

SAR 1,081 total

includes taxes & fees

3 Dec - 4 Dec

Two large well-appointed bedrooms are separated by wonderful bathroom.

"Everything was great.. this is our 5th time staying here. we absolutely love the the laidback vibe of the entire property! "

"This is our second time staying at this house. Just like the first time, it was clean and well-stocked, and the communication with the owner was great and responsive. We come to Medford to see family; this house is in a great location and quiet. We will definitely stay again on our next trip! "

"Very charming home with everything you need to relax and enjoy a vacation in Ashland, Oregon."

SAR 1,892 total

includes taxes & fees

3 Dec - 4 Dec

"Easy access to nearby attractions. And, you can just walk into town for a coffee, or bite to eat."

"We have stayed there twice now. Our art gallery reception was last night in Medford. Today I visited a friend in Ashland. Debbie’s Diner is very close for breakfast and Starbucks down the road. The house has an elegant feel to it, high ceilings and lots of windows to the backyard. Thank you so much."

SAR 1,937 total

includes taxes & fees

29 Nov - 30 Nov

"Every detail thought of for an enjoyable stay. "

SAR 1,963 total

includes taxes & fees

24 Nov - 25 Nov

"This house is in a very nice, quiet neighborhood but really centrally located to surrounding amenities. A beautiful and clean home - love the way it is decorated!! Jill was a great host. Her response time to any communication was almost instant."

"We loved this house so much. The views were absolutely amazing. We did stargazing at night and watched the sunrise out there. Beautiful house with great windows. Relaxing and quiet spot!"

"Cozy home, we had a wonderful stay. Close to Crater lake and the airport which was important to us. Plenty of room and a beautiful view "

"Mike and Mindy's place had everything we could ask for and more."

SAR 762 total

includes taxes & fees

23 Nov - 24 Nov

"Tremendously happy to have discovered this jewel of a getaway! A peaceful paradise with a wonderful cabin to comfort us during our stay. There really is nothing better than the sound of pouring rain dancing on the roof top while listening to the snap-crackle-and-pop of the woodstove warming us up while we sip on hot chocolate with marshmellows..ahhh, relaxation at its best. And what a great host we had! Mich greeted us upon our arrival and instantly made us feel truly welcomed. She gave us a...

SAR 2,966 total

includes taxes & fees

1 Dec - 2 Dec

"My husband and I have stayed at many of the rentals in Ashland over the years. We really enjoyed the location of Hellman House. One could walk just about anywhere to dine, have drinks, shop, visit famous Lythia Park. The home was clean, and the property manager was very responsive. My only nitpicky thought is that the upstairs bedroom doesn’t have a door. Kind of odd. Should be easy enough to add one. Our daughter and her fiancé stayed with us two nights, and so we had to be quiet downstairs as...

SAR 1,201 total

includes taxes & fees

24 Nov - 25 Nov

"This was perfect for our needs. We needed a place to stay while spending time with our family, so we didn't spend much time at the home. It's right on a busy road. The house itself is clean and basic. Appreciate being able to have our dog with us. "

SAR 938 total

includes taxes & fees

23 Nov - 24 Nov

"We came to Medford for high school graduation. We had 4 adults, 1 child and 1 dog staying with us. We were pleasantly surprised the moment we walked in on just how big this place was. The back yard was heaven for a nice warm weekend. The neighborhood is quiet and well kept. This house has everything you need and has great vintage character. Definitely family friendly. This location is close to everything you need and made our trip easy. The check in and check our process was so simple that I...

"We enjoyed the home. "

"Clean. Tidy. comfortable. Well appointed. But we left a pair of walking polls behind and would like Sugar to keep them for us and we will pick them up when we stay again in the fall of 2025. David Roberts"

"Such a warm, inviting and cozy home! My family had such a wonderful time! We really enjoyed the beautiful pool, the large kitchen, and the open floor plan that made the family room our great meeting & games place! The owners are wonderful human beings! We can’t wait to visit again!"